(E)-4-methyl-1-phenylpent-2-ene-1,4-diol | 56539-58-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-4-methyl-1-phenylpent-2-ene-1,4-diol
• CAS: 56539-58-3
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: GTHFLGAFIBUEJI-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-methyl-1-phenylpent-2-ene-1,4-diol 在 Jones reagent 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 生成 1-(6,8-dihydroxy-4,4-dimethyl-2-phenyl-4,5-dihydro-2,5-methanobenzo[d][1,3]dioxepin-9-yl)pentan-1-one
  参考文献：
  名称：

  Concise Construction of the Tricyclic Core of Bullataketals Enabled by a Biomimetic Intermolecular (3 + 3) Type Cycloaddition

  摘要：

  A remarkable TFA-mediated method for the construction of a biologically interesting tricyclic ketal skeleton was uncovered by starting from a variety of readily available acylphloroglucinol and diacylphloroglucinol substrates. This approach, which mimics a biosynthetic olefin isomerization/hemiacetalization/dehydration/(3 + 3) type cycloaddition sequence through a 2H-furan-1-ium intermediate, establishes a viable synthetic strategy for efficient synthesis of bullataketals analogs.

  DOI：

  10.1021/acs.orglett.5b01970
• 作为产物：
  描述：

  甲基(2E)-4-羰基-4-苯基丁-2-烯酸酯 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成 (E)-4-methyl-1-phenylpent-2-ene-1,4-diol
  参考文献：
  名称：

  Concise Construction of the Tricyclic Core of Bullataketals Enabled by a Biomimetic Intermolecular (3 + 3) Type Cycloaddition

  摘要：

  A remarkable TFA-mediated method for the construction of a biologically interesting tricyclic ketal skeleton was uncovered by starting from a variety of readily available acylphloroglucinol and diacylphloroglucinol substrates. This approach, which mimics a biosynthetic olefin isomerization/hemiacetalization/dehydration/(3 + 3) type cycloaddition sequence through a 2H-furan-1-ium intermediate, establishes a viable synthetic strategy for efficient synthesis of bullataketals analogs.

  DOI：

  10.1021/acs.orglett.5b01970

文献信息

• Atom-Transfer Radical Addition of Alcohols to Aliphatic Alkynes
  作者：Yingxia Xiao、Zhong-Quan Liu

  DOI：10.1021/acs.joc.9b00804

  日期：2019.8.2

  An intermolecular hydrogen bond-promoted atom-transfer radical addition of simple alcohols to aliphatic alkynes is demonstrated here. Through this strategy, a variety of allyl alcohols can be synthesized in high selectivity and yields. Furthermore, this work reveals the relationship between selectivity and the substrate.

  在此证明了单醇的分子间氢键促进的原子转移自由基加成到脂肪族炔烃上。通过这种策略，可以高选择性和高产率合成多种烯丙醇。此外，这项工作揭示了选择性与底物之间的关系。
• Concise Construction of the Tricyclic Core of Bullataketals Enabled by a Biomimetic Intermolecular (3 + 3) Type Cycloaddition
  作者：Haibo Tan、Hongxin Liu、Xinzheng Chen、Yunfei Yuan、Kai Chen、Shengxiang Qiu

  DOI：10.1021/acs.orglett.5b01970

  日期：2015.8.21

  A remarkable TFA-mediated method for the construction of a biologically interesting tricyclic ketal skeleton was uncovered by starting from a variety of readily available acylphloroglucinol and diacylphloroglucinol substrates. This approach, which mimics a biosynthetic olefin isomerization/hemiacetalization/dehydration/(3 + 3) type cycloaddition sequence through a 2H-furan-1-ium intermediate, establishes a viable synthetic strategy for efficient synthesis of bullataketals analogs.